[(1S,4R,9R,10R,13R,14R)-14-hydroxy-5,5,9-trimethyl-14-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methyl 6-nitronaphtho[1,2-e][1,3]benzodioxole-5-carboxylate

Details

• Internal ID: 54eebd11-26f5-4466-ac76-5eea0396ab05
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Aristolochic acids and derivatives
• IUPAC Name: [(1S,4R,9R,10R,13R,14R)-14-hydroxy-5,5,9-trimethyl-14-tetracyclo[11.2.1.01,10.04,9]hexadecanyl]methyl 6-nitronaphtho[1,2-e][1,3]benzodioxole-5-carboxylate
• SMILES (Canonical): CC1(CCCC2(C1CCC34C2CCC(C3)C(C4)(COC(=O)C5=CC6=C(C7=C5C(=CC8=CC=CC=C87)[N+](=O)[O-])OCO6)O)C)C
• SMILES (Isomeric): C[C@@]12CCCC([C@H]1CC[C@]34[C@H]2CC[C@H](C3)[C@](C4)(COC(=O)C5=CC6=C(C7=C5C(=CC8=CC=CC=C87)[N+](=O)[O-])OCO6)O)(C)C
• InChI: InChI=1S/C36H41NO7/c1-33(2)12-6-13-34(3)27(33)11-14-35-17-22(9-10-28(34)35)36(39,18-35)19-42-32(38)24-16-26-31(44-20-43-26)30-23-8-5-4-7-21(23)15-25(29(24)30)37(40)41/h4-5,7-8,15-16,22,27-28,39H,6,9-14,17-20H2,1-3H3/t22-,27-,28+,34-,35+,36+/m1/s1
• InChI Key: NSKGDTVEJJFLRM-JAZARSDYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₁NO₇
• Molecular Weight: 599.70 g/mol
• Exact Mass: 599.28830265 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: 9.30
• Atomic LogP (AlogP): 7.95
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9417	94.17%
Caco-2	-	0.8271	82.71%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5345	53.45%
OATP2B1 inhibitior	+	0.5684	56.84%
OATP1B1 inhibitior	+	0.8618	86.18%
OATP1B3 inhibitior	+	0.9270	92.70%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9846	98.46%
P-glycoprotein inhibitior	+	0.7539	75.39%
P-glycoprotein substrate	+	0.5546	55.46%
CYP3A4 substrate	+	0.7353	73.53%
CYP2C9 substrate	-	0.6052	60.52%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	+	0.6092	60.92%
CYP2C9 inhibition	-	0.6710	67.10%
CYP2C19 inhibition	-	0.5933	59.33%
CYP2D6 inhibition	-	0.8308	83.08%
CYP1A2 inhibition	-	0.6181	61.81%
CYP2C8 inhibition	+	0.8295	82.95%
CYP inhibitory promiscuity	-	0.5322	53.22%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7300	73.00%
Carcinogenicity (trinary)	Non-required	0.5081	50.81%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.9280	92.80%
Skin irritation	-	0.7758	77.58%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	+	0.6746	67.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4220	42.20%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5679	56.79%
skin sensitisation	-	0.8384	83.84%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7507	75.07%
Acute Oral Toxicity (c)	III	0.5675	56.75%
Estrogen receptor binding	+	0.7856	78.56%
Androgen receptor binding	+	0.7690	76.90%
Thyroid receptor binding	+	0.5573	55.73%
Glucocorticoid receptor binding	+	0.7197	71.97%
Aromatase binding	+	0.7462	74.62%
PPAR gamma	+	0.6906	69.06%
Honey bee toxicity	-	0.7602	76.02%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.43%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.80%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.64%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.76%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.52%	96.77%
CHEMBL2581	P07339	Cathepsin D	95.41%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.40%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	92.97%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.93%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.61%	96.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	90.48%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.48%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	88.75%	90.17%
CHEMBL5028	O14672	ADAM10	87.09%	97.50%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	86.97%	92.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.84%	97.25%
CHEMBL3902	P09211	Glutathione S-transferase Pi	85.77%	93.81%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	84.42%	87.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.37%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.32%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.85%	100.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.39%	96.67%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.13%	97.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.97%	89.00%

Plants that contains it

• Aristolochia pubescens

Cross-Links

• PubChem: 101260746
• LOTUS: LTS0157323
• wikiData: Q105185094